


The Warrior and the Princess

by evansrogerskitten



Category: Dean Winchester - Fandom, Supernatural
Genre: Bondage, Dean dressed up as Negan, F/M, Halloween, NSFW, Oral Sex, Restraints, Smut
Language: English
Status: Completed
Published: 2018-10-29
Updated: 2018-10-29
Packaged: 2019-08-09 16:53:36
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,160
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16453745
Author URL: https://archiveofourown.org/users/evansrogerskitten/pseuds/evansrogerskitten
Summary: Jack convinces you and the Winchesters to dress up for Halloween, which leads to festivities you could only have hoped for.





	The Warrior and the Princess

**Author's Note:**

> For SPN Kink Bingo Square Filled: Bondage. Also for Followers Autumn Challenge, prompt: Halloween.

Jack had begged for weeks about going out for Halloween.

“Puhhhlease?” He harassed you and Sam one morning. You’d only had half of a cup of coffee and weren’t ready to look through the case files in front of you, let alone bargain with the kid.

Sam sighed heavily. “You know what, you get Dean to agree, then we’ll go. Right?” He turned to you.

“If we don’t have a case by Halloween, then okay,” you snorted, scrolling through email on your laptop. “Go ask Dean.”

Jack grinned and bounded down the hallway. Ten minutes later you could hear Dean grumbling as they approached the War Room. “Kid, every day is Halloween for us.”

“Yeah, but Y/N said if we don’t have a case then we can go!” Jack pointed at you as they came around the corner.

Dean’s eyes narrowed on you. Neither you or Sam said anything, so Dean finally sighed and looked over at Jack.

“Okay, if we don’t have a job, we’ll go,” he conceded, “but I’m not dressing up.”

“You have to!” Jack exclaimed. “It’s Halloween, my first one! Well, my first one than we can celebrate. Right Y/N?”

“Oh, I never agreed to dressing up,” you replied. Jack’s shoulders dropped and you suddenly felt bad for him. It would make him so happy. Just wait until he found out about all the nougat filled candy. “Okay Jack, you get Sam and Dean to dress up, I will too.”

Sam snickered, “You get Dean to dress up, I will too.”

Dean groaned and threw his hands up. “Fine! We’ll go!”

“Yes! I’ll go find costumes for us!” Jack disappeared.

“There’s no way I’m letting him dress me,” Dean said as he turned on his heel, pausing to look back at you. “And no couples costumes!”

“Okay,” Sam replied sullenly. Dean was still cursing at you both as he huffed his way down the hall, leaving you and Sam snickering as you searched for a new case.

* * *

Jack must’ve arranged some magical monster repellent because a few days later, there was no case to be solved and the four of you were going to the Lebanon Fright Fest. Jack originally wanted the four of you to be the characters from Wizard of Oz, but Dean shot that down before you could even sarcastically suggest Sam should be Dorothy.

You were just going to wear jeans, a plaid, and one of Dean’s Stetsons and go as a cowgirl but Jack was insisting you wear the costume he got for you.

“Jack, I am not wearing this,” you apprehensively inspected the shiny red, blue and gold costume. It was kind of cute but so short. It was freaking freezing at night already and there was no good place to hide your bowie knife.

“Why not? Just please try it. I got this just for you.” Jack petted the vinyl and then looked up at you with puppy dog eyes that Sam really should stop teaching him. “You’re Wonder Woman to me.”

“Kiss ass.” You rolled your eyes but couldn’t help but smile. “When you say stuff like that I have to!”

Jack clapped his hands. “Yes! Be ready in twenty minutes!” Before you could ask about his costume he was out the door.

You quickly dressed in the blue and gold skirt and red bodice, matching belt, and arm band. You glared at the tiara and left it on the counter, leaving your hair down and wavy instead of pulling it back like usual. Once you had it all on you had to admit that your legs looked great. Wonder Woman was totally badass too. Your knife slid into your boot and you attached the gold boot covers to hide the handle. You actually looked kinda hot.

Jack was yelling for you down the hallway so you grabbed your heavy jacket and hurried to the War Room. Sam was leaning against the map table, looking down at his phone. You laughed when you saw the black monogrammed cape over his shoulders and wand on the table.

“Really Sam? Harry Potter?”

Sam shrugged, slipping his phone into his pants pocket. “It was this or Jon Snow.”

“So a cape either way?” You laughed. “Good luck picking up chicks in that, Gryffindor.”

Jack was rustling with something in the center of the library.

“Where’s your costume, Jack?”

The boy grinned as he heaved an inflatable T-Rex costume into the War Room. “It’s a dinosaur!”

You and Sam both laughed, helping him lift the nylon animal shell so Jack could step into it. “There’s no way you’ll fit into the Impala like this.”

“So we’ll put him in the trunk.”

You glanced over your shoulder at Dean with a smile, and then did a quick double take. Your jaw dropped as you looked him over, Jack’s costume long forgotten. Black boots, dark gray jeans, a few leather belts, a thick black leather jacket with silver zippered pockets, a red scarf, and to top it all off, a baseball bat wound with barbed wire.

“What…” you stared at him. “Did you...”

Dean strolled towards you and you swallowed hard at the sway of his hips. “You like that zombie show, so I figured what the hell. And you think that Negan guy is hot, right?”

You nodded, biting your lip as you traced the front zipper with your finger. “I...I like this. A lot.”

“Cool, so I’m him,” Dean smiled. “Even if he is old enough to be our da-”

“Let’s GO!” an inflatable dinosaur suddenly interrupted. With a wink Dean lead you out to the garage, Jack and Sam right on your superheroine heels.

Jack’s dinosaur costume had to go in the trunk after all to his dismay. But once you parked at the festival’s gravel lot Sam helped him back into it. While the two of them were struggling to get the tail straight Dean leaned against the hood next to you and shot you the bright smile that made you forget your own name for a second.

“Wonder Woman?”

You shrugged and smiled as you smoothed down the skirt. “Jack picked it out.”

Dean nodded, plump lower lip tucked under his teeth as he looked you up and down. “Your legs look hot.” He reached up and scratched the back of his neck awkwardly. “You look hot.”

“Thanks,” you blushed and straightened the costume belt. You knew that mischievous look usually lead to mind blowing sex. When you looked back up he was still watching you. You and Dean weren’t official, you weren’t a “thing” as Sam would say as he rolled his eyes at you both. You were best friends, roommates, hunting partners...who just happened to have amazing sex every once in awhile. Occasionally after stressful hunts, whiskey fueled and heated all night. Once on Christmas, a mistletoe inspired make out leading to dirty talk. That one time you two were stuck in the cave overnight in Oregon and it was rainy and your breath got all steamy and the way his moans echoed off the cave walls.

Yeah. Really amazing unforgettable sex. But Dean didn’t need to know that you thought about being with him all the time. He didn’t need to know that you wanted more. You were his badass friend with an amazing sex benefit. That was why he was looking at you like he couldn’t wait to find out what was under your polyester armor.

“RAWR!” Jack rambled around the car, his grin visible through the clear vinyl panel in the front. Your group headed into the gates to Fright Fest; Negan, Harry Potter, Wonder Woman, and a Tyrannosaurus Rex out for a night of fun.

Three hours of rides, haunted houses, hard apple cider, and laughter were exactly what you all needed. Jack jostled around the lot with two other T-Rexes around his physical age and Sam actually met a girl, a cute Tinkerbell named Robin. He was smiling wider than you’d seen in a long time, maybe ever since you met the boys.

For the most part you and Dean walked around and people watched. The two of you did waste thirty bucks using fake rifles trying to shoot fake vamps in a carnival game that you both made super competitive. When a dead clown jumped out at you in the Nightmare Manor Dean laughed and wrapped his arm around you to stop your screaming, and then teased you relentlessly for twenty minutes. And when you were cold he looped the red scarf from his costume around your neck. There were constant butterflies in your stomach as the tension between the two of you built. It felt more like a date than just a night off from hunting.

At the third haunted house you put down your foot in protest, refusing to go to any more so Dean suggested heading back to the bunker. To your surprise Sam stayed at the fair with Tinkerbell and Jack. You knew Sam would send Jack back home when it was time for Sam to make his late night plans.

The drive home was too long, Zeppelin playing quietly and Dean’s arm wrapped tight around your shoulder. Once you were home Dean lead you to his bedroom door, his lips not leaving yours as he peeled your denim jacket off. You pulled at the zipper on his coat, revealing the white v-neck tee underneath.

“You ready to go, darlin’?” He teased as he pushed the door shut and then walked you back towards the bed.

“I love it when you call me that,” you replied breathlessly, watching his every move as he shed his costume. He wasn’t some zombie killer on TV, Dean was a real hunter. But with the mischievous gleam in his eyes and the pronounced swagger as he followed you to the bed, you could almost see a resemblance to the guy on tv.

Dean’s lips crashed against yours as he laid you beneath him. You moaned into his mouth as his hands grabbed your wrists and held them down, anchoring you so that he could kiss and bite your neck.

“Dean.” You tugged at his grip and felt his mouth turn into a smile as it roamed over your pulse.

“Whatcha want, darlin?” he asked as he looked down at you.

You smirked, your eyes darkening. “I like it when you hold me down like that.”

“Yeah?” He grinned, his hands pushing your wrists into the pillow a little harder. “Want me to tie you up?”

You nodded, clenching your thighs to try to control the throb in your core. Dean bit his lip and nodded, and you watched with wide eyes as he undid the two thick leather belts he was wearing as part of his costume.

“Gimme your wrist,” he ordered. You held up your left wrist so he could wrap the belt around it and then the bed frame. He did the same to the other and then nodded as you tugged and tested them.

“You want out just say “Halloween”, ‘k?” He grinned. You nodded, raising your head to meet his kiss. His fingers pushed your corset down, revealing your bare breasts.

“God you look so hot,” he groaned. Dean’s voice was already deep and gravelly, but aroused it became as deep as a wolf’s growl.

Like he was unwrapping a gift he moved down to lift the short skirt, revealing the red boy shorts that barely covered you. “Mmmm,” he nibbled on his bottom lip as his fingers traced the top stitch on the cotton. His eyes widened as he watched a small spot on the front of the cotton darken. “You gettin’ off from me just lookin’ at you?”

“Yeah,” you groaned and dropped your head back on the mattress, your wrists still pulled back. Dean chuckled and pulled one side of your underwear down, and then the other. The rough calluses on his fingers skimmed down your thighs, the friction sweet against your soft skin. You opened your eyes and watched as he pulled the white t-shirt over his head and then kicked off his boots, leaving him in the dark gray jeans and black boxers. Your chest was heaving as he dropped down onto his stomach between your legs.

Dean’s hands pushed the costume skirt up and then rested on your hips as he kissed your inner thighs, watching as you twisted your hips up to meet his mouth.

“Oh god,” you groaned loudly as Dean sucked at your folds, licking you open and nuzzling your sensitive skin with his scruffy chin. He was much more aggressive than usual, and you didn’t know if it was because of his inner Negan or his mood, but you didn’t care. He ate you out like he was going to run out of time, his mouth sucking and licking, nibbling and kissing until you were trembling.

“Keep doing that,” you instructed, your hands in tight fists as his lips latched onto your clit. Your fingers ached to anchor into his hair and pull. You were moaning loudly with each suck of his lips, and when Dean moved a hand from your hip to slide two fingers inside you nearly fell apart.

“C’mon princess,” he encouraged. You moaned at the new pet name and clenched your thighs around his ears, reveling in the pulse inside you. Your arms thrashed as you tried to pull away from the restraints, and with a scream you came all over Dean’s face, clenching around his fingers and tongue as you collapsed boneless and sated.

“You good?” Dean asked as he sat up on his knees, a hand running down his scruffy chin to wipe away your cum.

“Mmhmm,” you nodded, drunk on the sex and him. “Want you. Fuck me.”

Dean smirked. “Don’t have to ask me twice.”

Within a minute he was naked and on top of you. You whined underneath him and he pulled away from the kiss, worry lining his forehead and brow. “What’s wrong?”

“My costume,” you replied, using your chin to point to the offending fabric. “I can’t take it off if you’ve got me all tied up.”

“Ummm,” Dean looked down at the dress, his fingers running down the seam of the bodice reverently. “Wear it for me?”

Your hummed in agreement, your pussy clenching around nothing. “Wonder Woman kink, huh?”

“Oh shut up, Miss Bondage,” Dean teased as he stroked himself a few times, his mouth crashing down to yours for a kiss that made you forget all about the costume. He pulled you close to him, careful not to hurt your arms as he flipped the edge of the skirt up so he could watch his cock sink inside you.

“Christ, you are so tight,” he groaned into your ear, his hips lifting to slide back inside slowly. You clenched around him and he groaned again, his mouth covering yours as he started to fuck you.

“God you look so hot like this,” Dean marveled at you in the skimpy costume with your arms tied back, your breasts bare. “Should fuck you like this more often.”

You moaned and nodded. “Tie me up again?”

“Uh huh,” Dean nodded. “Fuckin’ take you.”

You wanted to wrap your arms around him, but the inability to move while Dean fucked you was almost as hot as the sex itself. Dean’s mouth strayed from your nipples to your neck, sucking dark marks and biting until you begged for him to fuck you harder. Your pussy was fluttering around him, wet and hot as his cock rammed into you.

“Dean,” you wrapped your legs around his waist and held on to the restraints, both of you moaning as you gave way to the pleasure. “I’m gonna,” you moaned, the belts stretching from your pull. “Dean.”

“Yeah, me too.” Dean slammed into you harder with a deep groan, his cock hitting your G-spot and sending you over the edge. “Come for me, princess.”

“Fuck!” you moaned as your orgasm hit you, your body arching underneath him as the power of it rolled through you. Dean’s hips staggered once more before his body stiffened on top of yours and he spilled hot cum inside you, a low moan vibrating from his chest matching your high one.

He laid on top of you for a few minutes, the two of you sweaty and out of breath. You whimpered when you arms started to ache, the lack of endorphins revealing the tingly pain of your arms falling asleep.

“Oh, sorry,” Dean stood up hastily to undo the belts and set your wrists free. He gently massaged each wrist and placed them next to your hips before flopping onto the bed next to you. The room was quiet for a while and you giggled when you straightened the cups of your bodice, still half dressed in the costume next to a naked Dean.

“You always wanted to fuck Wonder Woman, didn’t you?” You smirked as you turned on your side, your head held up in your palm.

“Yeah guess so. I always kinda had a crush on her when I was a kid,” he admitted. “She was always so badass.”

The room was quiet for a few more minutes before Dean tucked you next to him, his arm wrapping around you. “That’s a reason why I like you so much.”

“Why?” You held his gaze as he looked down at you.

Dean paused. “You’re badass. And not just for a chick or a superhero or somethin’. You’re just...awesome.”

“Oh,” you smiled, ecstatically cheering on the inside. You rested your hand on his bare chest and nodded. “I...you too.”

“Badass. Awesome. Really amazing in bed.” Dean chuckled but then as the sound faded away he took your hand, your fingers lacing together over his chest. “I know we’ve been kinda, like not a thing or whatever, and I didn’t know what to say but I really...I like you.”

You smiled. “Same.”

“Really?”

“Really,” you nodded and leaned in to kiss him. The kiss was hot, a current running underneath it that you’d barely just breached. “I like you too. A lot. Like cuz of the sex, but also cuz...it’s us, you know?”

“Yeah. Awesome,” Dean breathed. You snuggled up next to him, relieved and giddy that he felt the same way. “I do have a question for you.”

“What?” you asked, your fingers pausing on their trace of his sternum as you looked up warily.

“Ummm, can you keep the Wonder Woman costume?”

Your laughter was quieted by Dean’s mouth, your teasing silenced only when he peeled the costume off of you and shut you up with his tongue. Laying there in Dean’s arms, you never would've guessed it would’ve been Wonder Woman and Negan that made you finally admit how you felt. Turns out getting dressed up for Halloween was a really good idea after all.

**Author's Note:**

> FEEDBACK MEANS THE WOLRD TO ME! KUDOS AND COMMENTS ARE APPRECIATED 
> 
>  
> 
> Do not copy and paste my writing anywhere without my consent. This work is property of evansrogerskitten. Characters aren’t mine, but this fanfiction is. These works contain material protected under International and Federal Copyright Laws and Treaties. Any unauthorized reprint or use of this material is prohibited. No part of these works may be reproduced in any form or by any means, electronic or mechanical, including photocopying, recording, or by any information storage and retrieval system without express written permission from the author / publisher. An electronic reference link to the original posted work may be provided for purposes of promotion or assistance of publication by the readers discretion, if proper credits are given to the author in the re-post.


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